N-(4-chlorophenyl)-2-(2-methyl-quinazolin-4-ylthio)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(4-chlorophenyl)-2-(2-methyl-quinazolin-4-ylthio)acetamide
• 英文别名: N-(4-chlorophenyl)-2-(2-methylquinazolin-4-yl)sulfanylacetamide
• 化学式: C₁₇H₁₄ClN₃OS
• 分子量: 343.837
• InChiKey: CPLWDBOWZBMZBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-4(3H)-喹唑酮 在 劳森试剂 、 甲醇 、 氢化钾 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-(4-chlorophenyl)-2-(2-methyl-quinazolin-4-ylthio)acetamide
  参考文献：
  名称：

  2-Alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides: synthesis, molecular docking, antimicrobial and anticancer properties

  摘要：

  In this study, a series of novel 2-alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides were synthesized and evaluated for antimicrobial and anticancer activities. Their structure was confirmed by elemental analysis and spectral data (FT-IR, LC-MS, H-1-NMR). Antimicrobial activity was tested in vitro against Staphylococcus aureus, Enterococcus faecalis, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, Candida albicans and NCI in vitro preliminary anticancer activity against nine different cancer types. The most active antibacterial and antifungal compounds were: 2.1, 2.2 and 2.4. The introduction of the carboxylic acid or amide residue into the fourth position of quinazolin-4(3H)-thione resulted in the absence of antimicrobial activity. Substance 3.8 inhibited renal cancer UO-31 line and 2.18 - leukemia CCRF-CEM. The results of in silico molecular docking for DHFR and CK2 kinase had no correlation with in vitro properties, proposing the presence of other biological activity pathways.

  DOI：

  10.3109/14756366.2015.1018243

文献信息

• 2-Alkyl(aryl)-quinazolin-4(3<i>H</i>)-thiones, 2-R-(quinazolin-4(3<i>H</i>)-ylthio)carboxylic acids and amides: synthesis, molecular docking, antimicrobial and anticancer properties
  作者：Lyudmyla Antypenko、Sergiy Kovalenko、Yulia Posylkina、Vladyslav Nikitin、Natalia Fedyunina、Vitalii Ivchuk

  DOI：10.3109/14756366.2015.1018243

  日期：2016.3.3

  In this study, a series of novel 2-alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides were synthesized and evaluated for antimicrobial and anticancer activities. Their structure was confirmed by elemental analysis and spectral data (FT-IR, LC-MS, H-1-NMR). Antimicrobial activity was tested in vitro against Staphylococcus aureus, Enterococcus faecalis, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, Candida albicans and NCI in vitro preliminary anticancer activity against nine different cancer types. The most active antibacterial and antifungal compounds were: 2.1, 2.2 and 2.4. The introduction of the carboxylic acid or amide residue into the fourth position of quinazolin-4(3H)-thione resulted in the absence of antimicrobial activity. Substance 3.8 inhibited renal cancer UO-31 line and 2.18 - leukemia CCRF-CEM. The results of in silico molecular docking for DHFR and CK2 kinase had no correlation with in vitro properties, proposing the presence of other biological activity pathways.